Hydrochloric Acid → HCID 178441263, 화합물

HRID 1888650노트

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HRID 1888650 반응식
[CH2:1]([C:5]1=[CH:6][N:7]([C:25]([CH3:28])([CH3:27])[CH3:26])[S:8]/[C:9]/1=[N:10]\[C:11]([C:13]1([CH3:24])[CH2:17][CH2:16][CH:15]([C:18]([O:20]C)=[O:19])[C:14]1([CH3:23])[CH3:22])=[O:12])[CH2:2][CH2:3][CH3:4].[OH-].[K+].C(O)C.Cl>O>[CH2:1]([C:5]1=[CH:6][N:7]([C:25]([CH3:26])([CH3:28])[CH3:27])[S:8]/[C:9]/1=[N:10]\[C:11]([C:13]1([CH3:24])[CH2:17][CH2:16][CH:15]([C:18]([OH:20])=[O:19])[C:14]1([CH3:23])[CH3:22])=[O:12])[CH2:2][CH2:3][CH3:4]

참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 14797Potassium HydroxideHCID 178441264HCID 178441264, 화합물

생성물 1

HCID 178441263HCID 178441263, 화합물수율 75%

시약·촉매·용매 1

HCID 962Water용매

반응 조건

온도
60 °C

실험 절차

To a 20-mL scintillation vial containing a magnetic stir bar were added the product from Example 92C (102 mg, 0.250 mmol) and potassium hydroxide (84 mg, 1.50 mmol). Ethanol (1 mL) and water (0.25 mL) were added. The vial was heated to 60° C. and the reaction mixed for 24 hours. After cooling to room temperature, the pH was adjusted to ˜1 by addition of 1N hydrochloric acid. The mixture was extracted with dichloromethane (3×10 mL). The combined organic extracts were dried (MgSO4), filtered, and concentrated by rotary evaporator to afford a tan solid. The product was recrystallized from ethyl acetate/hexanes to afford 74 mg (75%) of the title compound. 1H NMR (DMSO-d6) δ ppm 0.63 (br s, 3H), 0.91 (t, J=7.3 Hz, 3H), 1.23-1.38 (m, 8H), 1.57-1.68 (m, 12H), 1.76-1.87 (m, 1H), 2.00-2.11 (m, 1H), 2.65-2.84 (m, 4H), 8.7 (br s, 1H), 11.7 (br s, 1H). MS (ESI+) m/z 395 (M+H)+.

후처리

  1. additionTo a 20-mL scintillation vial containing a magnetic stir bar
  2. additionthe reaction mixed for 24 hours
  3. temperatureAfter cooling to room temperature
  4. extractionThe mixture was extracted with dichloromethane (3×10 mL)
  5. dry with materialThe combined organic extracts were dried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated by rotary evaporator
  8. customto afford a tan solid
  9. customThe product was recrystallized from ethyl acetate/hexanes

출처 및 근거

ORD 기록
ord-222f79c7092c47fe83de71c02f9557d2
출처 데이터셋
uspto-grants-2013_08
특허 번호
US08501794B2

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